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Synthesis 1989; 1989(7): 534-536
DOI: 10.1055/s-1989-27308
DOI: 10.1055/s-1989-27308
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(±)-erythro-γ,δ-Dihydroxycarboxylic Acid Lactones from a β-Lithiopropionate Equivalent and α-Chloroaldehydes
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Publication Date:
17 September 2002 (online)
Reaction of β-ethylthio-β-lithioacrylate 1A with α-chloroaldehydes furnished predominantly the erythro products 3, which were isolated as γ-lactones 4. At room temperature intermediates 3 are transformed into the (±)-erythro-γ,δ-dihydroxycarboxylic acid γ-lactones 8. Raney nickel treatment provided interesting natural γ-lactone derivatives; thus, from erythro-8c the socalled L-factor erythro-9c was obtained. Similarly, from β-methoxy β-lithioacrylate 10A the (±)-erythro-γ,δ-dihydroxycarboxylic acid δ-lactone erythro-11 was gained.